Annapolis Sailing Charters: Sailing Chesapeake Bay

We have just the right boat for you and your crew...

Choose from a large fleet of quality yachts

Annapolis sailing charters offer something for everyone from family fun to romantic moonlit nights. Any of our modern monohulls to exciting innovative catamarans will have you cruising from Annapolis in comfort and style. Choose your bareboat charter or add full services for a luxury sailing charter experience.

Sailing Charters From Port Annapolis

Annapolis Bay Charters is located at The Port Annapolis Marina on Back Creek. This full-service marina offers a pool, private bathhouses, breakfast/sandwich shop, picnic/grilling areas, water-taxi service to downtown shops and restaurants, and ample parking. At anytime during your charter, you may come back to use your slip and the facilities at no additional cost. Back Creek offers easy access to the Chesapeake Bay to get your sailboat charter vacation started quickly.

Frequently Asked Questions

What is a 'Bareboat Charter'?

The concept of a “bareboat charter” – a boat rental without captain or crew – is very simple: A family or group of friends makes a reservation for a boat in advance, board the vessel at the designated time and place, receive a thorough check out of equipment and systems, and head to sea. During the charter period, the charterer determines the itinerary, sailing routes, destinations, etc. The charterer also assumes responsibility for the boat during the term of the contract; he or she acts as owner of the yacht.

What Sailing Experience Is Required?

Generally, the person skippering the vessel must have experience operating a boat of similar size (within five feet), displacement, and rig, and have comparable navigating experience to the planned itinerary. As part of the reservation process we discuss your experience. Our checkouts include a full systems checkout, and, if necessary, an underway check-out. We help you feel comfortable handling your yacht.

What is Included With the Boat?

Cabin amenities will vary depending on the yacht you choose, but all yachts will be equipped with standard basics. For example, all yachts will have a fully equipped galley, including cooking and dining necessities, coffee maker, BBQ grill, Coast Guard Safety Equipment such as Adult PFDs, flares, first-aid kit, tool kit, charts, cruising guide, binoculars, and flashlight. Bed linens, towels, and inflatable dinghies are not included, but available for an additional fee.

Are Captain and Crew Available?

If you prefer to hire a skipper of full crew, we have a list of qualified, experienced sailing professionals to choose from. Many people enjoy the security of having a captain aboard during the first few hours while they get their “sea legs” back. Others like to have that extra person aboard to help out throughout their trip.

How Do I Reserve My Charter?

To reserve the yacht of your choice, call us at 800-991-1776 to confirm availability. A 30% deposit will secure your reservation. We accept cash, check, Mastercard, Visa, or American Express. We will send a contract and Operator’s Manual by email. The balance is due 45 days prior to the charter.

What If I Must Cancel My Charter?

If the charter is cancelled more than 90 days prior to your departure date, then your deposit if fully refundable. If between 89 days and 45 days prior to the charter start, a fee of $100 will be charged for boats 29’ to 39’ and $150 for yachts 40’ to 50’ and all catamarans. If the charter is cancelled between 44-15 days prior to the charter’s inception, a cancellation fee of $500 (loss of deposit) for all yachts will be charged. If a charter is cancelled 14 days or less prior to departure, there will be no refund. There will be a $50 rescheduling fee if the charterer elects to move the charter in lieu of cancellation; this is subject to availability of another similar yacht and must be more than 15 days prior to departure. No charters will be cancelled or rescheduled due to inclement weather or rain. However, if a named windstorm occurs at the time of your charter, rescheduling is permitted at no charge.

What Additional Costs Should I Expect?

Additional expenses include fuel, holding tank pump-outs, provisioning, as well as the security deposit of either $1000 or $1500 depending on the size of the yacht chartered.

How Do I Provision My Charter?

You can provision your own charter. But, if you want more time on the water and less time preparing for your trip, we offer an online provisioning service option based on your selections and specific needs. Please inquire for details.

Are Dinghies and Linens Available?

Yes. We rent dinghies with outboard motors as well as linens and towels. Please consult your friendly charter reservationist for details.

May I Arrive The Evening Before My Charter Begins?

Yes, you may check in anytime after 4 PM local time the evening before your charter for an additional $150.00.

Where is Annapolis Bay Charters Office?

Our office and our fleet are located in the Port Annapolis Marina on Back Creek in Annapolis, Maryland. Back Creek is one creek east of the Annapolis Harbor/City Dock area. There is plenty of parking, a nice bathhouse, pool, a ship’s store for marine items, and a cafe that offers food and beverages. Address: 7080 Bembe Beach Rd #211A, Annapolis, MD 21403.

Worldwide destinations with Dream Yacht Charter

Sail the places you’ve only dreamed of. The Caribbean, the Mediterranean, the Indian Ocean, the Chesapeake Bay or the Pacific Ocean. With over 40 locations worldwide and more than 700 boats from which to choose, Dream Yacht Charter is everywhere you want to sail.

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Annapolis Bay Charters

At Annapolis Bay Charters, we are more than your everyday boat rental operation. We combine an impressive fleet of well-maintained sailboats and powerboats, a service-oriented staff with over thirty years experience, and a yacht charter location that makes it easy to visit some of the Chesapeake Bay's hidden gems.